Tetrahydrofuran → (4S)-1-(4-amino-1-methyl-1H-pyrazol-3-yl)-4-((tert-butyl(dimethyl)silyl)oxy)pyrrolidin-2-one

HRID 632749Notes

Reaction equation

HRID 632749 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][N:12]([C:14]2[C:18]([N+:19]([O-])=O)=[CH:17][N:16]([CH3:22])[N:15]=2)[C:11](=[O:23])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1>[C].[Pd].CO>[NH2:19][C:18]1[C:14]([N:12]2[CH2:13][C@@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2])[CH2:10][C:11]2=[O:23])=[N:15][N:16]([CH3:22])[CH:17]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 131735443(4S)-4-((tert-butyl(dimethyl)silyl)oxy)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one

Product 1

HCID 131735444(4S)-1-(4-amino-1-methyl-1H-pyrazol-3-yl)-4-((tert-butyl(dimethyl)silyl)oxy)pyrrolidin-2-oneYield 93.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of (4S)-4-((tert-butyl(dimethyl)silyl)oxy)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one (2.7 g), 10% palladium-carbon (0.85 g), THF (27 mL) and methanol (27 mL) was stirred at room temperature for 2 hr under hydrogen atmosphere. The reaction mixture was filtered through a membrane filter, and the filtrate was concentrated under reduced pressure to give the title compound (2.3 g).

Workup

  1. filtrationThe reaction mixture was filtered through a membrane
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bd4e943725e24e7fb6a054ae4ac1291f
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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